Enantioselective microbial hydrolysis of dissymmetrical cyclic carbonates with disubstitution

Abstract

Enantioselective microbial hydrolysis of C 1 and C 2 dissymmetrical cyclic carbonates with disubstitution (methyl and another groups) has been developed. Pseudomonas diminuta (FU0090), a bacterium, efficiently catalyzes the hydrolysis of five-membered cyclic carbonates. While the trans-substrates are hydrolyzed with low enantioselectivities and/or reactivities, the microbe hydrolyzes the cis-substrates with very high enantioselectivities to afford the corresponding almost optically pure anti-(2 R,3 S)-diols. On the other hand, six-membered trans-cyclic carbonates are enantioselectively hydrolyzed to afford the corresponding optically active syn-(2 R,4 R)-diols, although the hydrolysis of the cis-substrates gives racemic compounds. In all cases, the enzyme prefers the ( R)-enantiomer for the carbon atom bearing a methyl group.